Action of Methylmagnesium Iodide on Cholesterol α-Oxide and 6-Ketocholestanol

1951 ◽  
Vol 73 (10) ◽  
pp. 4660-4662 ◽  
Author(s):  
Louis F. Fieser ◽  
Jean Rigaudy
Keyword(s):  
Methylmagnesium Iodide

ChemInform Abstract: ACTION OF METHYLMAGNESIUM IODIDE ON DIOXOLANONES

1978 ◽  
Vol 9 (7) ◽  
Author(s):  
M. BERCOT ◽  
G. JEANTY ◽  
P. BERCOT
Keyword(s):  
Methylmagnesium Iodide

1,4-DIMETHYLBICYCLO[2.2.1]HEPTANE DERIVATIVES

1965 ◽  
Vol 43 (8) ◽  
pp. 2306-2311
Author(s):  
Peter Yates ◽  
Thomas R. Lynch
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Acetic Acid ◽  
Sulfuric Acid ◽  
Magnetic Resonance ◽  
Methylmagnesium Iodide ◽  
Nuclear Magnetic Resonance Spectra ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The product from the action of methylmagnesium iodide on bicyclo[2.2.1]heptane-2,5-dione gave 2-exo-5-endo-diacetoxy-1,4-dimethylbicyclo[2.2.1]heptane on treatment with sulfuric acid in acetic acid. This has been converted to 1,4-dimethylbicyclo[2.2.1]heptane-2-exo-5-endo-diol, to 1,4-dimethylbicyclo[2.2.1]heptane-2,5-dione, and to 1,4-dimethylbicyclo[2.2.1]heptane-2-endo-5-endo-diol. The stereochemical assignments have been made on the basis of the interpretation of the nuclear magnetic resonance spectra of these compounds. The exo–endo diacetoxy compound is shown to be the expected product from a double Wagner–Meerwein rearrangement.

ChemInform Abstract: Characteristics of the Reaction of Methylmagnesium Iodide with Perfluorocarboxylic Acid Esters.

ChemInform ◽  
1988 ◽  
Vol 19 (45) ◽  
Author(s):  
D. V. BATIZAT ◽  
A. A. YAROSH ◽  
A. V. IGNATENKO ◽  
V. A. PONOMARENKO
Keyword(s):  
Perfluorocarboxylic Acid ◽  
Methylmagnesium Iodide ◽  
Acid Esters

The synthesis of meso-Hexoestrol[3,4-D2] and some related specifically deuterated compounds

1974 ◽  
Vol 27 (8) ◽  
pp. 1743 ◽  
Author(s):  
DJ Collins ◽  
JJ Hobbs
Keyword(s):  
Methyl Ketone ◽  
Sodium Hydride ◽  
Dimethyl Sulphoxide ◽  
Reduction Sequence ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Methylmagnesium Iodide ◽  
High Yields ◽  
Unsaturated Nitrile ◽  
Hofmann Elimination

Condensation of p-methoxyphenylacetonitrile with p-methoxypropiophenone in the presence of sodium hydride in dimethyl sulphoxide at 65� gave (Z)-(23%) and (E)-2,3-bis(p-methoxyphenyl)pent-2-enenitrile(16%). The reduction of this α,β-unsaturated nitrile with lithium aluminium deuteride in tetrahydrofuran, and workup with D2O or with H2O, gave high yields of erythro-2,3-bis(p-methoxy-phenyl)valeronitrile[2,3-D2], or -[3-D], respectively. Conversion of the dideuteronitrile into the corresponding methyl ketone with methylmagnesium iodide, followed by a hydride reduction-tosylation-hydride reduction sequence, then demethylation, afforded meso-hexoestrol[3,4-D2]. Dehydration of (3RS,4SR)-3,4-bis(p-methoxyphenyl)hexan-2ξ-ol[3,4-D2] with phosphoryl trichloride in pyridine gave 3,4-bis(p-methoxyphenyl)hex-2-ene[4-D]. Reduction of erythro-2,3-bis(p-methoxy- phenyl)valeronitrile[3-D] to the corresponding amine followed by quaternization and Hofmann elimination afforded 2,3-bis(p-methoxypheny1)pent-1-ene[3-D].

Methyl exchange on silicon during the addition of methylmagnesium iodide to a cyanohydrin O-silyl ether

1999 ◽  
pp. 431-432 ◽  
Author(s):  
Cécile Arbez-Gindre ◽  
Valérie Berl ◽  
Jean-Pierre Lepoittevin
Keyword(s):  
Silyl Ether ◽  
Methylmagnesium Iodide
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